High refractive index material

Patent metadata

Field	Value
Publication number	US-10030168-B2
Application number	US-201314400844-A
Country	US
Kind code	B2
Filing date	Mar 7, 2013
Priority date	May 14, 2012
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

A high refractive index molecule and high refractive index polymers comprising such monomers. The high refractive index monomer comprises a carrier atom having a high refractive index group attached thereto, the high refractive index group comprising a heterocyclic compound comprising at least one sulfur atom.

First claim

What is claimed is:

1. A polysiloxane polymer or copolymer having a siloxane backbone and comprising a group derived from a molecule comprising a carrier atom and a high refractive index functional group, the molecule having the formula:

where W is the carrier atom, R 1 is independently chosen from hydrogen, hydroxyl, or a group containing C1-C30 carbon atoms chosen from a linear or branched alkyl radical, a linear or branched alkoxy radical, an alkylvinyl radical (including allyl), a cycloalkyl radical, a branched or linear alkenyl radical, a cycloalkenyl radical, a linear or branched alkynyl radical, an aryl radical, a substituted aryl radical, or a polynuclear aromatic group; A is chosen from a high refractive index group comprising a sulfur-containing heterocyclic structure having 2 or 3 sulfur atoms in a single ring structure; B is chosen from a halide, alkoxy (OR), hydroxyl, an alkylvinyl radical (including allyl), hydrogen, —(CH 2 ) n SH, —(CH 2 ) n NH 2 , a glycidyl radical, or a combination of two or more thereof; W is silicon; n is 1-10; x is at least 1; y ranges from zero to two less than the valence of the carrier atom; z is at least 1; 1≤x+y≤one less than the valence of the carrier atom; and x+y+z is equal to the valence of the carrier atom; and
wherein the sulfur-containing heterocyclic structure-containing repeating units are present in an amount of from 0.1 to 40 mol % based on the total number of repeating units in the polymer.

2. The polymer of claim 1 , wherein the carrier atom of the molecule is incorporated into the backbone of the polymer and the high refractive index functional group is pendent to the carrier atom.

3. The polymer of claim 1 having a refractive index of at least 1.42.

4. The polymer of claim 1 having a refractive index of at least 1.50.

5. The polymer of claim 1 having a refractive index of at least 1.55.

6. The polymer of claim 1 having a refractive index of at least 1.60.

7. The polymer of claim 1 having a refractive index of from 1.42 to about 1.65.

8. The polymer of claim 1 , wherein the polymer is described by the formula
M 1 k M 2 j D 1 a D 2 b D 3 d D 4 e T 1 c T 2 i Q f   (4)

where M 1 and M 2 are independently R 2 R 3 R 4 SiO 1/2 ; D 1 , D 2 , D 3 , and D 4 are independently R 5 R 6 SiO 2/2 ; T 1 and T 2 are independently R 7 SiO 3/2 ; Q is SiO 4/2 ; R 2 -R 7 groups are independently chosen from hydrogen, hydroxyl, a linear or branched alkyl radical, a linear or branched alkoxy radical, an aryl radical, an alkylvinyl radical, amide, amino-groups, propyl-mercapto groups, glycidyl-containing groups, a high refractive index sulfur-containing heterocyclic structure, or a high refractive index molecule pendant group, where at least one of R 2 -R 7 is chosen from (1) A, optionally R 1 in Formula 1, or (2) the sulfur-containing heterocyclic structure; a is from 1-1000, b is from 0-500,c is from 0-500, d is from 0-100, e is from 0-100, f is from 0-100, k is from 1-1000, j is from 0-1000, and i is from 0 to 200.

9. The polymer of claim 1 , wherein the polymer is described by the formula MD a D OL d D H e T c Q f M, M H D a D Ph b D OL d D H e T c Q f M H , M H D a D Ph b D OL d T c Q f M H , MD a D OL d D vi g T c Q f M, M vi D a D OL d D vi g T c Q f M vi , or M vi D a D OL d T c Q f M vi , where M represents a trialkylsiloxy radical or a dialkylvinylsiloxy, Q is SiO 4/2 ; T is R 7 SiO 3/2 where R 7 is independently chosen from hydrogen, hydroxyl, a linear or branched alkyl radical, a linear or branched alkoxy radical, an aryl radical, an alkylvinyl radical, amide, amino-groups, propyl-mercapto groups, glycidyl-containing groups, a high refractive index sulfur-containing heterocyclic compound, or a high refractive index molecule pendant group, where at least one of R 7 is chosen from (1) a high refractive index heterocyclic molecule of Formula 1, or (2) a sulfur-containing heterocyclic compound; D OL represents an alkylsiloxy comprising a high refractive index monomer, D H represents an alkyl hydrogen siloxy, D vi represents alkylvinylsiloxy, D represents dialkylsiloxy, M vi represents a dialkylvinyl siloxy, M H represents a dialkylhydrogen radical, and a, b, c, d, e, f, and g are positive integers.

10. A composition comprising the polymer of claim 1 .

11. The composition of claim 10 , wherein the polymer is a copolymer comprising polydimethyl siloxane, polydiphenysiloxane, or polymethylphenylsiloxane.

12. The composition of claim 10 , where the composition is a curable siloxane composition.

13. The curable composition of claim 12 further comprising an antioxidant.

14. The curable composition of claim 12 further comprising a thermal stabilizer.

15. The curable composition of claim 12 further comprising a UV stabilizer.

16. The curable composition of claim 12 further comprising an adhesion promoter.

17. The curable composition of claim 12 further comprising a platinum group metal catalyst in an amount of about 1-100 ppm.

18. The curable composition of claim 12 further comprising an inhibitor.

19. The curable composition of claim 12 further comprising a filler.

20. The composition of claim 10 , wherein the composition is a coating composition.

21. The composition of claim 10 , where the composition is chosen from an antireflection coating, a conformal coating, a paint formulation, and a personal care product formulation.

22. A device comprising the composition of claim 10 .

23. The device of claim 22 , where the device is chosen from a light emitting diode, an organic light emitting diode, a laser diode, a waveguide, an optical computing device, an optical storage medium, an optical lens, a microlens, a paint formulations, a gradient refractive index optical component, and a dynamic gradient refractive index components.

24. The polymer of claim 1 wherein the amount is from about 2.5 to about 30 mol %.

25. The polymer of claim 1 wherein the amount is from about 5 to about 25 mol %.

26. The polymer of claim 1 wherein the amount is from about 10 to about 20 mol %.

27. A composition comprising a copolymer having siloxane backbone and comprising:
(a) polydimethyl siloxane, polydiphenysiloxane, or polymethylphenylsiloxane; and
(b) a group derived from a molecule comprising a carrier atom and a high refractive index functional group, the molecule having the formula:

where W is the carrier atom, R 1 is independently chosen from hydrogen, hydroxyl, or a group containing C1-C30 carbon atoms chosen from a linear or branched alkyl radical, a linear or branched alkoxy radical, an alkylvinyl radical (including allyl), a cycloalkyl radical, a branched or linear alkenyl radical, a cycloalkenyl radical, a linear or branched alkynyl radical, an aryl radical, a substituted aryl radical, or a polynuclear aromatic group; A is chosen from a high refractive index group comprising a sulfur-containing heterocyclic structure having 2 or 3 sulfur atoms in a single ring structure; B is chosen from a halide, alkoxy (OR), hydroxyl, an alkylvinyl radical (including allyl), hydrogen, —(CH 2 ) n SH, —(CH 2 ) n NH 2 , a glycidyl radical, or a combination of two or more there

Assignees

• Momentive Performance Mat Inc

Inventors

• Srivastava Rajiv
• Dukes Douglas Michael
• Lin Hai Hui

Classifications

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08K5/0091

  Complexes with metal-heteroatom-bonds · CPC title

• C09D183/04 Primary

  Polysiloxanes · CPC title

• C07F7/0814

  said ring is substituted at a C ring atom by Si · CPC title

• C08G77/38

  Polysiloxanes modified by chemical after-treatment · CPC title